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Croatica Chemica Acta, Vol. 90 No. 1, 2017.

Original scientific paper

https://doi.org/10.5562/cca3111

Synthesis, Antimicrobial Activities of New Sulfonamidobenzoxazoles and Molecular Docking Studies on Escherichia coli TEM-1 β-Lactamase

Tugba Ertan-Bolelli ; Department of Pharmaceutical Chemistry, Ankara University, Faculty of Pharmacy, Ankara, Turkey
Kayhan Bolelli ; Department of Pharmaceutical Chemistry, Ankara University, Faculty of Pharmacy, Ankara, Turkey
Suzan Okten ; Department of Pharmaceutical Microbiology, Trakya University, Faculty of Pharmacy, Edirne, Turkey
Fatma Kaynak-Onurdag ; Department of Pharmaceutical Microbiology, Trakya University, Faculty of Pharmacy, Edirne, Turkey
Esin Aki-Yalcin ; Department of Pharmaceutical Chemistry, Ankara University, Faculty of Pharmacy, Ankara, Turkey
Ismail Yalcin ; Department of Pharmaceutical Chemistry, Ankara University, Faculty of Pharmacy, Ankara, Turkey

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Abstract

β-Lactam antibiotics are frequently used for treatment of multi-drug resistant microbial infections and the most common mechanism of resistance against these antibiotics is bacterial β-lactamase production. Herein, we reported the design, synthesis and in vitro antimicrobial activities of some new 2-substituted-5-(2,4-dinitrophenylsulfonamido)benzoxazole derivatives. Compounds TN1, TN2, and TN3 were found to be significantly active against E. coli isolate which contains extended spectrum β-lactamase enzyme at the MIC value of 8 µg mL–1 and that is
4-fold higher than the reference drug ampicillin. We performed molecular docking studies into active site of Escherichia coli TEM-1 β-lactamase enzyme in order to predict the protein-ligand interactions. According to the docking results, compounds TN1, TN2, and TN3 showed strong interactions between the important active site residues which are responsible for the catalytic mechanism of TEM-1 β-lactamase enzyme and a good correlation is found with the experimental data.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

antimicrobial activity; benzoxazole; Escherichia coli; β-lactamase; molecular docking; sulfonamide

Hrčak ID:

182676

URI

https://hrcak.srce.hr/182676

Publication date:

2.1.2017.

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